Phenyl isocyanate → 5-Oxo-6-(3-phenyl-ureido)-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

HRID 1824430Notes

Reaction equation

HRID 1824430 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:17])[CH:11]([NH2:16])[CH2:12][CH:13]=[CH:14][CH2:15][CH:8]2[CH2:7][CH2:6]1)=[O:4].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:17])[CH:11]([NH:16][C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:26])[CH2:12][CH:13]=[CH:14][CH2:15][CH:8]2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 695845816-Amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

Product 1

HCID 695842975-Oxo-6-(3-phenyl-ureido)-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester, 8, (120 mg, 0.5 mmol), phenyl isocyanate (110 μL, 1 mmol) and triethyl amine (200 μL) are stirred in CH2Cl2 (10 mL) at room temperature. After complete consumption of starting material, the reaction is poured into 1 N HCl; washed with brine; and dried of sodium sulfate. The organics are evaporated and the residue is purified over silica (40% ethyl acetate: hexane). The desired product is obtained as a clear oil. 1H NMR (CDCl3): δ 7.81 (s, 1H), 7.35 (m, 2H), 7.23 (t, J=7.3 Hz, 2H), 6.98 (t, J=7.4 Hz, 1H), 6.85 (bs, 1H), 5.81 (m, 2H), 5.28 (m, 1H), 4.52 (dd, J=8.9, 2.5 Hz, 1H),4.27 (m, 1H), 3.58 (s, 3H), 2.95–2.82 (m, 2H), 2.45 (m, 1H), 2.29 (m, 1H), 2.16–1.96 (m, 4H). 13C NMR (CDCl3): δ 173.0, 172.4, 155.8, 139.4, 129.1, 129.0, 126.2, 122.8, 119.9, 60.6, 58.9, 52.1, 51.3, 34.9, 33.1, 33.0, 27.5. ESI MS: 358.15 (M+H).

Workup

  1. customAfter complete consumption of starting material
  2. additionthe reaction is poured into 1 N HCl
  3. washwashed with brine
  4. dry with materialand dried of sodium sulfate
  5. customThe organics are evaporated
  6. customthe residue is purified over silica (40% ethyl acetate: hexane)

Sources & evidence

ORD record
ord-9daca458d3b245b69b8716c69e4622f1
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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